I had slipped into the club, in the old Bossanova space on East Burnside Street, curious about all this urban cowboy business. At the door, the bouncer gave my ID a quick glance and informed me that "Salsa is on the second floor." After a short pause he continued, "and there's Cowboy Karaoke on the third floor, if you're interested."

I took no offense, understanding that—although I could be mistaken for Dwight Yoakam—160-pound guys with long blonde hair rarely qualify for cowboy-hood. But that doesn't mean I was not qualified for Cowboy Karaoke.

I grew up in Tomah, Wis., a small farming and military town where country is king. For most of my childhood, Willie Nelson and Alabama accompanied me and my family on semiweekly trips in our brown 1981 Oldsmobile to the nearest theater in a town 45 miles away. My mother had an unhealthy obsession with Randy Travis, and my dad was fond of belting out Hank Williams Jr. songs. Every once in a while the school bus driver would play Z93, but the event was rare, and if songs such as INXS' "Need You Tonight" came on, the station would be immediately flipped to country on WCOW 97.1.

When I finally scored my own stereo, things started to change. With control of the radio, I tuned into 107.5, the classic-rock station out of Nielsville and discovered Jimi Hendrix, Led Zeppelin and Kansas. While still in the firm grasp of redneck culture, I was finding something in "Castles Made of Sand" and "Immigrant Song" that I couldn't find in "Boot Scootin' Boogie" and "Louisiana Saturday Night." By the time I got my license, I was fully divorced from my wannabe cowboy neighbors, choosing instead to be a wannabe Kurt Cobain. I still listened to some bad music. I still went to every Tomah Indians football game. I would even follow the line of cars to the postgame party in the middle of some field where everyone would get wasted while songs sung by millionaires with cowboy hats blared out of a Ford F-150. But I refused to sing "Friends in Low Places."

Until tonight. Back at Outlaws, a lone table of hipsters in this sea of cowboy hats has adopted me, and two of them are on stage singing the Garth Brooks song everyone knows. Later a burly gent with a handlebar mustache sings Hank Williams Jr.'s "Family Tradition," and again I'm singin' along: "Why do you drink?/ Why do you roll smoke?"

"How do you know this song?" says my new acquaintance Amy. "You're one of them." She laughs and I smile, thinking that maybe she's a little right. Then, after a rousing rendition of Big & Rich's "Save a Horse (Ride a Cowboy)," which I do not sing along with, my name is called and I go up to sing "Mama, Don't Let Your Babies Grow Up to Be Cowboys."

Feeling cocky and clever from the whiskey, I start the third chorus, singing "Mama, don't let your babies grow up to be hipsters/ Don't let 'em wear white belts and..." but before I can continue on with "drive El Caminos," the karaoke DJ gets on his mike and blurts "Sing the song!" Staring at me from under the brim of his cowboy hat, he is noticeably angry. And I, again, am nervous.